-
1
-
-
33644973407
-
-
For recent reviews, see: and references therein
-
For recent reviews, see: J. W. Blunt, B. R. Copp, M. H. G. Munro, P. T. Northcote, M. R. Prinsep, Nat. Prod. Rep. 2006, 23, 26-78, and references therein.
-
(2006)
Nat. Prod. Rep.
, vol.23
, pp. 26-78
-
-
Blunt, J.W.1
Copp, B.R.2
Munro, M.H.G.3
Northcote, P.T.4
Prinsep, M.R.5
-
2
-
-
30744433322
-
-
For recent reviews, see: and references therein
-
For recent reviews, see: Y. Hamada, T. Shiori, Chem. Rev. 2005, 105, 4441-4482, and references therein.
-
(2005)
, vol.105
, pp. 4441-4482
-
-
Hamada, Y.1
Shiori, T.2
Rev, C.3
-
3
-
-
33845224207
-
-
DOI: 10.1002/ange.200602047
-
Y. Nakao, S. Yoshida, S. Matsunaga, N. Shindoh, Y. Terada, K. Nagai, J. K. Yamashita, A. Ganesan, R. W. M. van Soest, N. Fusetani, Angew. Chem., DOI: 10.1002/ange.200602047;
-
Angew. Chem.
-
-
Nakao, Y.1
Yoshida, S.2
Matsunaga, S.3
Shindoh, N.4
Terada, Y.5
Nagai, K.6
Yamashita, J.K.7
Ganesan, A.8
Van Soest, R.W.M.9
Fusetani, N.10
-
4
-
-
33845199114
-
-
DOI: 10.1002/anie.200602047
-
Angew. Chem. Int. Ed., DOI: 10.1002/anie.200602047.
-
Angew. Chem. Int. Ed.
-
-
-
6
-
-
24744444744
-
-
b) M. Biel, V. Washolowski, A. Giannis, Angew. Chem. 2005, 117, 3248-3280;
-
(2005)
Angew. Chem.
, vol.117
, pp. 3248-3280
-
-
Biel, M.1
Washolowski, V.2
Giannis, A.3
-
7
-
-
20344392202
-
-
Angew. Chem. Int. Ed. 2005, 44, 3186-3216;
-
(2005)
Angew. Chem. Int. Ed.
, vol.44
, pp. 3186-3216
-
-
-
8
-
-
0242522928
-
-
c) T. A. Miller, D. J. Witter, S. Belvedere, J. Med. Chem. 2003, 46, 5097-5116; note that the HDAC inhibition profiles observed for azumamides E and C contradict the assumption that carboxylic acids at the "zinc binding" domain give poor enzymatic activity. See Ref. [4b].
-
(2003)
J. Med. Chem.
, vol.46
, pp. 5097-5116
-
-
Miller, T.A.1
Witter, D.J.2
Belvedere, S.3
-
10
-
-
0038340749
-
-
for recent reviews, see: and references therein
-
for recent reviews, see: M. Lei, M. P. Sibi, Tetrahedron 2002, 58, 7991-8035, and references therein.
-
(2002)
Tetrahedron
, vol.58
, pp. 7991-8035
-
-
Lei, M.1
Sibi, M.P.2
-
11
-
-
33845216327
-
-
note
-
Experimental procedures and spectroscopic data can be found in the Supporting Information.
-
-
-
-
12
-
-
33845196886
-
-
note
-
The acetylation was necessary for purification purposes.
-
-
-
-
13
-
-
33845224465
-
-
note
-
The enantiomeric excess of compound 11 was evaluated by Mosher ester analysis of the alcohol resulting from acetate hydrolysis (see Supporting Information).
-
-
-
-
14
-
-
0034803598
-
-
A. B. Benowitz, S. Fidanze, P. L. C. Small, Y. Kishi, J. Am. Chem. Soc. 2001, 123, 5128-5129.
-
(2001)
J. Am. Chem. Soc.
, vol.123
, pp. 5128-5129
-
-
Benowitz, A.B.1
Fidanze, S.2
Small, P.L.C.3
Kishi, Y.4
-
15
-
-
0141632651
-
-
D. R. Williams, K. Shamim, J. P. Reddy, G. S. Amato, S. M. Shaw, Org. Lett. 2003, 5, 3361-3364.
-
(2003)
Org. Lett.
, vol.5
, pp. 3361-3364
-
-
Williams, D.R.1
Shamim, K.2
Reddy, J.P.3
Amato, G.S.4
Shaw, S.M.5
-
16
-
-
33845232403
-
-
note
-
Compound 20 was easily prepared from commercially available ethyl 4-bromobutyrate.
-
-
-
-
17
-
-
0034676323
-
-
K. Uwai, K. Ohashi, Y. Takaya, T. Ohta, T. Tadano, K. Kisara, K. Shibusawa, R. Sakakibara, Y. Oshima, J. Med. Chem. 2000, 43, 4508-4515.
-
(2000)
J. Med. Chem.
, vol.43
, pp. 4508-4515
-
-
Uwai, K.1
Ohashi, K.2
Takaya, Y.3
Ohta, T.4
Tadano, T.5
Kisara, K.6
Shibusawa, K.7
Sakakibara, R.8
Oshima, Y.9
-
18
-
-
0033515510
-
-
M. Zhao, J. Li, E. Mano, Z. Song, D. M. Tschaen, E. J. J. Grabowski, P. J. Reider, J. Org. Chem. 1999, 64, 2564-2566; the oxidation reaction on 24 proved to be capriciously batch-dependant. It is reported therein that the presence of carbon-carbon double bonds can be troublesome. Two-step procedures (from the alcohol to the aldehyde and from the aldehyde to the carboxylic acid) gave yields of less than 30%. Fewer problems were observed for the oxidation of 30 (Scheme 5).
-
(1999)
J. Org. Chem.
, vol.64
, pp. 2564-2566
-
-
Zhao, M.1
Li, J.2
Mano, E.3
Song, Z.4
Tschaen, D.M.5
Grabowski, E.J.J.6
Reider, P.J.7
-
19
-
-
0037460144
-
-
M. P. Glenn, M. J. Kelso, J. T. A. Tyndall, D. P. Fairlie, J. Am. Chem. Soc. 2003, 125, 640-641.
-
(2003)
J. Am. Chem. Soc.
, vol.125
, pp. 640-641
-
-
Glenn, M.P.1
Kelso, M.J.2
Tyndall, J.T.A.3
Fairlie, D.P.4
-
20
-
-
0041475925
-
-
For recent reviews on peptide cyclizations, see: a) J. W. Davies, J. Pept. Sci. 2003, 9, 471-501;
-
(2003)
J. Pept. Sci.
, vol.9
, pp. 471-501
-
-
Davies, J.W.1
-
21
-
-
0036254144
-
-
and references therein
-
b) P. Li, P. P. Roller, J. Xu, Curr. Org. Chem. 2002, 6, 411-440, and references therein.
-
(2002)
Curr. Org. Chem.
, vol.6
, pp. 411-440
-
-
Li, P.1
Roller, P.P.2
Xu, J.3
-
23
-
-
0027406662
-
-
b) J. Dudash, Jr., J. Jiang, S. C. Mayer, M. M. Joullie, Synth. Commun. 1993, 23, 349-356.
-
(1993)
Synth. Commun.
, vol.23
, pp. 349-356
-
-
Dudash Jr., J.1
Jiang, J.2
Mayer, S.C.3
Joullie, M.M.4
-
24
-
-
33845209771
-
-
note
-
In the macrolactamization reaction, the reagents DPPA (the successor of the conventional "azide" coupling methods) and FDPP (inducing the formation of an activated pentafluorophenyl ester) are preferred to carbodiimide-based coupling reagents, whose urea group is difficult to remove (the only exception is the water soluble carbodiimide, EDC), and to "uronium" activators (for the concurrent end-capping through tetramethylguanidylation of the amino group).
-
-
-
-
25
-
-
85004721004
-
-
see
-
Using DPPA and BOP-Cl [bis(2-oxo-3-oxazolidinyl)phosphinic chloride (see: C. van der Auwera, M. J. O. Anteunis, Int. J. Pept. Protein Res. 1987, 29, 574-588), we observed the formation of trace amounts (ESI-MS analysis) of the cyclotetrapeptide 34 (see Supporting Information).
-
(1987)
Int. J. Pept. Protein Res.
, vol.29
, pp. 574-588
-
-
Van Der Auwera, C.1
Anteunis, M.J.O.2
-
26
-
-
33845227526
-
-
note
-
3OD solutions (see Supporting Information).
-
-
-
|